We sat down with Scott Clary, host of the Success Story podcast (100M+ downloads) to break down what it actually takes to reinvent your career.
Scott didn’t follow the traditional path. He questioned it.
In this conversation, we go deep on why curiosity is the starting point for any reinvention – and how most people stay stuck simply because they never stop to ask: is this even what I want?
We also get practical. If you’re mid-career, successful on paper, but feeling out of alignment, Scott shares how to navigate that tension without making reckless decisions. You’ll hear:
- Why the old career playbook no longer works
- The “die every night” exercise to get clear on what you actually want
- Why confidence (and control) matters more than talent
- How to take action without quitting your job overnight
- The truth about entrepreneurship: hard, but not complicated
This is a grounded, no-BS conversation about what it really looks like to take ownership of your career, and build something that actually fits your life.
If you’ve been thinking about making a change but haven’t started yet, this is your push.
We are BIG fans of Scott’s newsletter and we highly encourage you to click this link and sign up to receive consistent drops of gold from him!
If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook, learn more about us, and start creating what’s next!
**Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.
Episode Transcript
Scott: I would make the argument that everybody, whether or not you’re reinventing yourself, you are an entrepreneur, or you wanna succeed in a traditional, employee context, you have to adopt these traits. You have to think like an entrepreneur, especially in 2026 and beyond
Chris: All right, Todd, what are we talking about for our reinventors today?
Todd: Well, Chris man, I don’t know if I could be more excited for a conversation than I am right now, because we have on the line someone I’ve been following and admiring for a long time. Scott Clary the creator of the Success Story podcast, which is simply huge. Okay? And a must listen for anyone interested in success and fulfillment and how to achieve that life while remaining authentic. And what I love most about Scott’s show is how human it is. And when I listen, it reminds me that it’s really the stories that inspire us. And so before we just dive into everything, Scott, I just want to say thank you for being here and to give you a warm welcome into our show.
Scott: Thank you for having me. I appreciate it, and congratulations kindred spirits for building up this podcast together, so I appreciate you so much.
Todd: That means a lot to me. I really appreciate that. And you know, the thing that really pops out about you to me, and I’ve been following you, like I said for a while, is that you are a true reinventor, right? You started your career in enterprise sales and marketing and you achieved a lot of success there, right?
You built global teams for a bunch of well-known organizations, but you always got the value of exploring side hustles. And you began building your personal brand by creating content and experimenting and eventually launching Success Story. And I know I said a moment ago that it’s a huge podcast, but I think we’re talking in the neighborhood of what, like 50 million downloads, is that right?
Scott: Yeah. A little bit north of that, but yeah.
Todd: North of 50 million.
Scott: Right now, we are pushing, almost a hundred in total. So we are hitting about 2.5 to 3 million across YouTube, old episodes, new episodes audio, per month.
Todd: It’s Incredible. We’re blown away. So it’s amazing that you’re on here with us and you’ve also interviewed so many incredible people, right? Like Guy Kawasaki and Grant Cardone, people that I love, and I really love that you pick their brains about success, going deeper into their personal stories, to not only learn tactics, but also help us understand what their foundational, mental approach for success is.
And so now that we have you on our show, we kind of wanna do the same thing with you, my man. And it’s really relevant because our focus is to help mid-career professionals think about how to reinvent themselves. And it can be challenging for our listeners because they have, for the most part years, or even decades of mental and behavioral programming that needs a reboot.
Okay? So I’d love to start with your story a little bit and understand, what your motivation was for leaving that comfortable, successful corporate life and like how you went about reinventing yourself. I think that would really be a great place to start.
Scott: Well first of all, thank you again for bringing me on. And I think that I was just very fortunate, from a very young age to question everything. I think that that’s one of my strongest skill sets and personality traits. Just having curiosity to, not just follow the path that I’ve been on, I’ve had laid out for me that my parents said was a good path, that my boss said, this is the way it’s always been done and whatever. And that curiosity has always led me to question, what am I working on? Is it fulfilling? Is it something that I really want to do long term? Is this what I want my life to look like? I ask those questions and have those conversations with myself more often than the average person, not because I’m better or worse.
So, to walk through my career, how curiosity played a role in shaping sort of what I do now, was looking at the life and the career that my dad and my mom had, and realizing that the playbook that they thought would work for them and did work for them and afforded them a great life and a nice house and a healthy and happy family. It didn’t take much digging to understand that that playbook doesn’t work as well for the modern day, especially knowledge worker who’s trying to figure out and navigate a career and make a certain amount of money and live in a expensive city and afford a home and start a family. So I think that the playbook that worked for many of our parents and grandparents, I don’t think it applies so well today to somebody who is just starting their career and even somebody who is later on in their career. The reality is you can’t afford a house really if you’re just starting out, unless you’re incredibly successful and maybe you’re a lawyer or a doctor. My dad bought his first house cash when he was 25 years old, detached home. That reality doesn’t exist anymore. He had a pension, set up for him by the government so that when he retired at 55, he’d make 70% of his best years until he died. That doesn’t exist anymore. So I think especially for younger people, and we’re gonna talk about people that are a little bit older, but for younger people, myself included, when I was starting my career, that playbook that our parents subscribed to, you put in the same amount of effort as what your parents put in. You go to the same school, you get the same job, and you get a lesser output, if that makes sense.
That was a little bit depressing and disheartening to me, but it also forced me to reevaluate, okay, how am I gonna pursue a career? What am I going to do? Am I just gonna get a nine to five? Maybe, but maybe there’s other ways to build a life. Right?
I think that was sort of like the inflection point that prompted the behavior of curiosity, which, you know, fast forward has now turned me into a full fledged entrepreneur. Built my own business, my own media company. So that’s more or less the mindset that I think has gotten me to where I am today. And I think that’s one of the most important takeaways from our chat wherever you’re at, in life. I think that just the answer to all of your problems is more curiosity, more self-reflection, more asking really tough questions.
How this could apply to someone later in their career. They realize that their life is going okay. They’re, they’re making good money, but the same problem that applies to somebody who’s just starting their career is starting to apply to you now. So you realize that cost of living is increasing and your salary’s not increasing in step with cost of living. So now you feel like the same money you were making five or 10 years ago really isn’t affording you the same quality of life as it used to, and now you’re trying to figure out, okay, well. What do I do next? Or maybe you’re at a point in your career where money isn’t even the concern. You just feel like you’ve been doing this thing for so long and it’s just not fulfilling you the same way it used to. And it’s very scary to think about restarting or going in a different direction.
And I will always give this advice to people and hopefully they listen to it when they’re a little bit younger, but at any stage, you can just restart, reinvent yourself, and it’s just better to do it sooner than later.
So I think that just by being a little bit more curious, and by making sure that what you’re doing in life, whether or not you’re just starting out or you’re 45, 50, make sure that it’s actually in alignment with who you are. I don’t know how else to say it. I think that a lot of midlife crises come from, people who just wake up and discover that they’re not in alignment, that they’ve never questioned whether or not the business they’re building or the life they’re living, or the person they’re with or the job they’re doing or whatever is actually what they want.
It’s them just following a path that was laid out by their parents, their guidance counselor their influences when they were much younger, and they never sort of stop and pause. So whether or not you’re older or younger, the first thing you have to do before you even think about how do I restructure my life, or how do I move in a different direction, or how do I make sure that I do something that I’m happy with and not blow up the rest of my life, is to give yourself space to think is the life that I’m living or the goals that I’m pursuing, are they even mine? I think that’s like where you start.
And then after you answer that question, then you can have the conversation about the how. How am I going to move into alignment? you know, I don’t want it to sound corny. It’s like there’s a lot of people that are working jobs that they really hate and they’re making good money. And if they complain, people are just gonna tell ’em to shut up. And like, you have a great setup, why are you looking a gift horse in the mouth,
Chris: Be grateful. Be grateful for this thing that you have.
Todd: That was you, man. Right? I mean, you know.
Chris: Yeah.
Scott: So, you know, you asked me about my story. And my story it started with curiosity. That was a gift that was sort of bestowed upon me.
I was blessed with that because my parents gave me the ability to be curious. And they said, you know what? Try whatever you want to try. That was such a gift. and then I just carried that personality through life. I’ve always just questioned everything.
You know, talk about my career. I was trying to find a traditional nine to five option that would make a little bit more money because I realized that most jobs don’t have pensions anymore.
My goal when I was starting my career was to sort of model the life of my parents. I think that’s what most of us want. If we had a good childhood. To replicate that for ourselves. And I couldn’t see an easy path to that. So I was like, let me just take more risks with my career. Let me see if I can go work in some companies that seemed that they would pay a little bit more than the government, right? That was like the goal. I start working in tech companies and then you start working in tech companies, and then I got exposed to more entrepreneurial people and, there was a few different things that happened in my life, but one of the companies that I worked for, I say startup, but it was like a 20-year-old startup, they were doing about $10 million in revenue, a hundred percent founder owned and operated. He built it from scratch and just the way he operated the stuff that he taught, he was like, purebred entrepreneur. And I just, I started to learn what entrepreneurship was. I started to learn what ownership was, what leverage was when he sold to private equity I started to understand what like an exit looks like. So you start to learn these things from people in your life just because I took a little bit of risk with my career, then I exposed myself to people that took even more risk. Then you’re curious about how they got to where they are.
You take those lessons and it’s almost like this flywheel and I mean, like, that’s why if you, if you hang out with, entrepreneur types, you’ll probably pick up a thing or two. But that’s really, that’s how my career got started. so I did tech, tech then moved into entrepreneurship.
And I’ve done so many different iterations of things that haven’t worked out, but I’ve done consulting. I’ve tried to launch communities. I tried to take a health and wellness supplement product to market. I have my podcast and I have an agency now, which is sort of my current version of entrepreneurship. I’ve invested in startups. I’ve tried to do a private equity play, by doing deal by deal SPVs. I’ve done like so many different things that I’ve tried to learn and take on and some success with, some not. but yeah, it just all started with curiosity. That was really really what got me going.
Chris: Scott, thank you so much. I mean, that’s first of all, you’re speaking words that have almost come outta my mouth as you’re telling that story when you talk about the people who just sort of follow the track of parents, guidance counselors and not even from a conscious perspective, the story I’ve told to Todd before on this podcast is I almost woke up as I was reaching 40 and asking that question that you said, where I’m like, who am I doing this for? Like, whose plan is this that I’m executing so dutifully. And I was doing very well, climbing the ladder, making money.
If I ever had any inkling out to anyone that like, this isn’t working for me, they were always like, what are you talking about? It’s great. Don’t rock the boat. So when I hear your story, I’m like, wow, I’m gonna encourage that curiosity in my kids because it sounds like you had a supportive space or environment there, and that makes a big difference.
You also had some wisdom at a really early age that I don’t think most people have the awareness to question or to just sort of, you were looking at things from a, from a macro level.
Scott: Very much. like, I’ve always been like a planner. Like, I always try and plan out my life, probably more than I should.
Like, you know, like all like ambitious, high performing people. We love like a certain element of control. And it’s actually sometimes to our detriment, because then it’s hard for us to like delegate stuff. But, I like routine, I like regimen, I like schedule. I like knowing where things are going. So at a super young age, I’m talking. 16, 17 years old, I’m thinking about, okay, so if I want the life of my family, how much money do I have to make to buy the house, have the white picket fence to, retire at 55 with no pension? Okay. That means that if I retire 55 with no pension, I need like 10 to $15 million in the bank somehow. And I have to sort of, as opposed to just getting paid out 70% of my best years until I die, now I gotta figure out how to accrue this bucket of money that’s gonna support me you know, from 55 to a hundred and how am I gonna make 10, $15 million? Like none of it aligns. And even that simple thought experiment of putting some numbers together, I think that’s stressing the hell out of a lot of young people as well as middle aged people who haven’t put thought towards investing, wealth building, like being strategic about their career.
I think this is stressing out a lot of people because I don’t think that many people really have a retirement plan at all.
Todd: Mm-hmm.
Scott: I think that most people were just drifting through life, they’re paycheck to paycheck. Sometimes they make more money than they find a way to spend that even more. And there’s some lifestyle creep in there too. But I don’t think a lot of people have a retirement plan because, that one entrepreneur that I mentioned before, who influenced me and was teaching me, or just exposing me to like what true entrepreneurship is. He would do things like, you know, lunch and learns, about how to invest in like the 401k and how to, pick different like investment options and that’s what I mean by being around the right people. So I was fortunate also to be in the right rooms. But I’ll tell you something. Even though I was fortunate to be around people like that, there was like 55, 60 people that worked for that company and I don’t think many of them took the same things away from what he was trying to teach as maybe a very select few, myself included.
You can expose yourself to these ideas, you can listen to this podcast, but ultimately it’s like just listening to the information and not
Todd: Taking the action.
Scott: That’s not gonna get you anywhere. So, you know, if I looked at like, the 55, whatever, 60 employees and thought, okay, how many of them who were sitting in the same rooms as me, tried to start their own thing or were more aggressive about their career, or learned how to invest to build wealth and not just tie your, your hourly to how much money you make. I would assume, less than 5% of the people that sat in that room really took it to heart and took it seriously.
So it’s not one thing, that got me from super safe, secure, W2, nine to five family, to completely just trusting myself and betting on myself, which is how I make money now. but it was all these ideas compounded over time that really helped.
Todd: Right. Okay. I love this, man. And so let me ask you a question now. And actually, when I asked this question, I want you to also call in all these amazing interviews that you’ve done with people that are like also very successful, right? Because you are a melting pot for all these different ideas. So a lot of our audience, especially these mid-career folks, right, you know, they’re in a position where they’re coming to reinvention because either they’re incredibly burned out, they don’t know what to do, or they’ve already started reinventing because they’ve been laid off, or they’re being disrupted by AI.
Scott: They were forced to reinvent.
Todd: There’s a lot of that Right now happening. Okay. A lot of these people, a lot of our audience have experienced a lot of success in life. You know, like on paper, based on what you said before, they followed the narrative that their parents laid out and they’ve had success, and now they’re being forced in some sense to reinvent right now. And so we did an episode that was called Do I need to Heal or Do I Need to Hustle? Okay? And, and it was breaking down this idea of, well, what is the process that I need to go through right now as I’m reinventing? Because it comes with two things. Number one, you called this self-reflection before. I need to self-reflect and get clarity about what is it that I do want or what would make me happy or successful, right?
I need to do that self-reflection. And at the same time, there’s this juxtaposition where, there’s a lot of pressure, especially for mid-career folks who have kids and have financial obligations and like need to recreate things really fast. I’m just curious, how would you talk to somebody like that who probably does need to do some self-reflection and healing work, but also has these very real pressures, how would you start coaching them, you know, and recommending them to think about reinventing?
Scott: So a few different exercises and we can talk about some mindset things and then some very tactical ideas. The first idea, if you are not reinventing yet, is to go through this process called die every night. What does that mean? It means that figuratively, not literally, when you go to bed at night, assume that that version of you has died and you wake up in the morning with no obligations. You don’t have to go to the job, you don’t have to build a business. You don’t have to even be married to the person that you’re with, figuratively. And for a moment, you just pause and you think, would I choose all these things today? Would I choose the person, the job, the business whatever? If the answer is no, that’s a signal that you have to start figuring out how to get back into alignment. And I think that it seems so obvious as most good advice is, but I don’t think many people pause and actually ask themselves that question. And it could mean that you are gonna repair your relationship with that thing, with your work, with your spouse, with your life. Or it could mean that you slowly have to move in a different direction, which is, that happens sometimes too. But I think that by getting ahead of it, you hopefully won’t wake up one day with a massive amount of resentment and blow up your life and then cause more stress.
So if you hate your job. Then ask yourself, why do you hate your job? Is it not enough money? Not the title, you know, you wanted to go work for FAANG but you’re working for some startup that nobody knows about. Like, why are you out of alignment? Your spouse, why are you not happy with your spouse anymore? Maybe it’s because you don’t date each other anymore. You never block off time. You know, you just become roommates basically. And maybe that means you go date more. Maybe it means you go to therapy maybe for your job, you’re more aggressive about, asking for a raise or you’re putting yourself out there and looking for position at another company.
There’s a million different ways to start to move in the right direction. But you have to understand where you wanna move first and why you wanna move. So that it’s not forced on you. That’s the goal. When things are forced on you, you’re making these manic last minute decisions, mostly out of emotion. Then that actually more often than not, causes more problems. So if you hate your job and you quit your job and you haven’t figured out how to make money, and now you have kids and mortgage, well, you’re gonna have a lot more stress and problems, and you’re gonna compound all these issues. If you wake up and you don’t like your spouse with this exercise, you can start to solve it.
Versus you are upset, you don’t feel connection, you go cheat, all of a sudden you’ve blown up your whole life, right? So it’s to get ahead of it. Now, if people have already gone through this process and they’re moving towards a goal, I hope this doesn’t sound too corny or cliche, but they have to have, confidence that they can actually do it. So, out of everybody who I’ve interviewed, there’s a concept, there’s a few words that I associate with this concept, but ultimately it’s ownership. Whether or not you call yourself high agency. Whether or not you, say that you have an internal locus of control, meaning that, you feel like you have control over everything that happens in your world, in your life. Anybody who I’ve interviewed has this concept and they believe that they have complete control over all outcomes. And like, it’s not just about control over outcomes, it’s about control over responses to outcomes.
But when you feel like you have this control in your life, it gives you permission to start moving in a direction that pulls you into alignment with what your career goals are. So if you hate your job, and you are really unhappy. If you feel like you truly feel like you can go build your own thing or you are owed more money or you deserve a better title. Like if you truly feel like you can make that thing happen, and you can reverse engineer how to get there, all of a sudden this transition phase becomes a lot less scary.
I think that the reason why transition is scary is because people are unsure as to whether or not they can actually do it. Because if they knew with a hundred percent certainty they could do it, they could quit their job, start the business, it was successful. Why would you be scared? The apprehension or the imposter syndrome is really because you just don’t believe you can do it. So if you adopt this idea of internal locus of control, you believe that you can accomplish anything and, and basically the world will bend to your will, if you adopt a couple other ideas, you have to find a way to understand the probability of the thing you’re trying to accomplish has a high likelihood of success because everything you’ve done in your life, you’ve succeeded at. This idea is important because more often than not, as humans, we just remember the things we failed at, not succeeded at. So if we keep record of all the times we’ve succeeded in our life, we can start to almost logic ourselves into understanding how competent and skilled we are and if we’ve succeeded at all these other projects and tasks. Why would we not be able to succeed at the next thing?
But more often than not, we forget all the things that we’ve been successful at and we focus on the time we didn’t get the job, or the time we got fired, or the time we got sued, or the time whatever, we focus on all these negatives because, that’s what sticks out.
But ultimately, for the average person, you are successful and you win 95% of the things that you go after. And like less than 5% are true failures. And when you understand that ratio, then all of a sudden the pivot or the career shift at any point in your life becomes a lot less scary. By the way, I’m spouting these off because these have had huge impacts on, on my life, but all these ideas are ideas that every single person that literally sits in that chair, across from me, believe in. They all are high agency individuals. They all believe they can impact the world.
They all believe that they’re lucky or successful or they understand how competent they are, which gives ’em the courage to go after the next thing. Another idea that’s important is to reverse engineer success. So I’m not just saying that you should believe you can do it and you should look at your past wins and just hope and pray that the next one’s gonna be a win.
I’m saying like, look at somebody who’s done it before and look at the steps they’ve taken to get there and start to map out those steps.
Todd: Model them
Scott: Just model them. And in the age of social media, like anybody who’s accomplished anything, loves to talk about it, they love to talk about exactly how they did it.
They’re gonna yap all day on podcasts and whatnot. So, I mean, like in my world, I talk to a lot of entrepreneurs who are trying to build a business. I’m assuming in your world you have people that are, in jobs looking to pivot and change what they’re doing. Could be another job, could be becoming an entrepreneur, whatever it is, it doesn’t matter. It’s the same concept. You want to make more money. You want to move into a new type of job. You want to build something that’s a hundred percent your own. Find somebody who’s done that and reverse engineer it.
If you’re a developer making $150,000 at a startup, and you hear about these, Facebook, Apple, Amazon, Netflix, Google Developers pulling in a million dollars per year and like, that’s what you want. You want prestige and you wanna work for FAANG and you wanna make, you know so much money, okay? So go research how to do that. Go research the skillset. Go research the questions they ask on the interview. I don’t know much. I’m not a developer, but it, I, I can guarantee you if I asked that question in Claude, or Chat GPT, it would give me a pretty good playbook, of the things that I have to do to move in that direction,
I would just take the steps that I know would move me in that direction. And the wild thing is if you put enough energy towards something, it has a funny way of actually working out.
Chris: You’re going through these things and I’m like, these are concepts that we talk about in some fashion that this is so useful and helpful. People need to hear this. One thing I just wanted to latch onto Scott, is it’s like what you’re talking about, I think is the essence of belief and effort.
In a sense where when people say, oh, I tried and it didn’t work. Right. I think what you’re talking about here is there’s an inevitability you can create when you truly believe I’m gonna figure this thing out. Nothing can stop me one way or another. The truth is, there is a reality of life. We might not hit the exact thing that we’re going for, but if you are inevitable about it, you are going to succeed.
It might be different than the way you might’ve envisioned it in the beginning, but you are going to get there. I always reflect back on myself where it’s like the jump across the chasm to get to what I really wanted was too daunting that, you know, there were a lot of false starts.
Oh I tried that, but it didn’t work out. But it’s not a real try. That’s kind of what is coming up for me as you speak about this Scott.
Scott: I like how you phrase it. There is an inevitability. That’s the perfect word.
I think that, you know, you mentioned a point where people try and they say they try and then they give up and they sort of fall back to their baseline or their comfort zone. I think that’s just a matter of expectation.
I think that we have incorrect expectations as to how long it’s gonna take, how hard it’s gonna be. I say this stuff, like, it’s easy. I think that’s the incorrect interpretation of what I’m trying to teach. It’s still going to be hard work. It’s gonna be exceptionally hard. But it’s not complicated. That’s the best way I can describe it. It’s hard, but not complicated.
Todd: Right. There’s a system here. There’s a system here that you can follow.
Scott: Well when I started a podcast. I just watch how other people put together their interviews, how they market their podcasts, how they structure their thumbnails on YouTube, the hook for their 45 second social clips, like i’m just studying. And I know that if I replicate enough, first of all, I’m gonna, achieve mastery in what I’m trying to do. I’m gonna be better at it. But also if I can get the same guests as Tim Ferris and I can ask just as smart questions as Tim Ferris and I can be such a good conversationalist. I’m not gonna be Tim Ferris, but I’m probably gonna be better than 99.9% of the podcasters out there.
Chris: Right.
Todd: Absolutely. Well said. And by the way, man, what are we doing right here? We’re modeling you. I mean, like we brought you on because we also wanna learn from you, right? So think one, one question around the entrepreneurship line, because a lot of folks that are in mid-career are now looking to what we’re talking about here.
Entrepreneurial projects, creative projects, because you know, the jobs just aren’t there anymore like they used to be. Okay? So we’re seeing a lot of that. I would say that’s probably 80 to 90% of our audience are people that are exploring different paths that maybe they didn’t even think would be exploring, let’s say five years ago. Okay. And so I love how you talk about this part of it that like, it’s inevitable, but it’s also hard. Okay.
And my question that I had written down before was, is there always elements of disappointment or even failure as you’re going out to explore entrepreneurial ventures and what is the mark of success?
Is it how resilient you are? Is it how smart you are? I know we’ve been bouncing around these ideas, but I wanna focus it particularly on, emerging entrepreneurs and people that are now thinking about starting, this is a big part of our audience and I think what you have to say here can really help.
Scott: Yes to all of it, but I think that failures are inevitable always. So I mentioned very briefly, even if you believe that, you can achieve anything. You’re still gonna have massive failures and setbacks that you feel like they’re outside of your control.
Like, I mean, we, we could talk about extreme circumstances where you quit your job, you’re building a business, you get into a car accident, you can’t work for six months. Like, I mean, like, well, how is that my fault? It’s not. But how you respond to that is entirely within your control. And even minor setbacks, if something doesn’t work in the business, how you respond to it and how you learn from it is entirely within your control.
And how you learn to not make that mistake again. So failure is inevitable. Especially if you’re doing anything that you’ve never done before. Like failure is actually the prerequisite to success. Like, you can’t have success without failure. You, you need failure to learn. And you have to learn yourself.
You will never really understand a lesson unless you go through the shit yourself, and that’s when you get it.
Another thing bringing it back to when we first started, curiosity. So you said like, do you have to be smart? No, you don’t have to be smart. You have to be curious. You have to be somebody who asks the right questions, who is always trying to break shit and do things differently. Like when you first start, you reverse engineer what someone else has done and then you figure it out and then you try and break it and then you learn what works better than what they’ve done. So I think that just being curious is a absolute superpower. Being a self-taught individual, so somebody that isn’t afraid of learning new skills and diving into new things that they’ve never ever looked into before. That’s the hallmark of a successful person. Whether or not you’re reinventing yourself, you are an entrepreneur, or you wanna succeed in a traditional, employee context, you have to adopt these traits.
You have to think like an entrepreneur, especially in 2026 and beyond. That could mean that even if you don’t wanna start a business, you have to be, messing around with LLMs. You have to be messing around with all these tools that we have access to right now, because at some point it’ll be very useful when you understand how to communicate with them, how to prompt them, how to, use them to 10x your output because, you know, maybe, maybe, you don’t get replaced by AI, but there’s a good chance for, especially for admin tasks especially for non-creative tasks and, people that are sort of just executing, AI is gonna be able to do that very, very soon.
So how do you make yourself 10x more efficient by leveraging these tools, even if you know, there’s no corporate mandate to do it.
That’s gonna help you keep your job in the future, it’s gonna help you land a new job. It’s gonna help you build a business. So like, if I was working in a company now, in my off time, I’d be messing around with, Claude and Chat, manis, which was acquired by Meta. Lovable, like, all these things are just fun little like side projects. But I just want to get a handle on what’s out there. And that’s the attitude that you gotta apply to your work, to your life. And when you start to go through life like an entrepreneur, the future is a lot less ambiguous when you feel like you have total control over your career. Like you, you know, if you get laid off, I know how to use AI. I could build an MVP for a product or a coaching or a consulting business. I know how to get clients. I know how to sell myself. I know how to use the latest tech. Like, it’s not so scary anymore when you think like an entrepreneur.
Chris: The phrase we use in this podcast a lot is be the CEO of your own life. And I think that that does apply within an organization, right? You don’t have to necessarily be an entrepreneur. It’s an entrepreneurial spirit. You talked before, you walked through a bunch of things that you said didn’t really work out for you right. As you were along this path, and you also said, it’s hard, but it’s not complicated. When we talk to the people in our community of reinventors, one of the things we try to encourage them to realize is that, when you’re going towards something with curiosity or you’re drawn towards it, not forced towards it, it does make it easier to burn the candle when you have to be doing the work late at night and like taking on these things on the side.
How much would you say like love of the work mattered to you, sort of as you’re leaning into what you’re doing and on the way up?
Scott: I don’t think love of the work mattered at all. I think understanding how the work tied to my personal North Star is what mattered. A lot of the work that I do sucks, especially before you can hire people.
Chris: Right.
Scott: By the way, everything I talk about, these are not just ideas that I’ve heard from other people. If you hear these ideas, test these ideas out in your own life understand when an idea makes contact with your reality. So what I’m saying is I always thought like an entrepreneur. I’ve always been very curious. I’ve always learned as much as I possibly can. When I started the podcast, I had no employees, so I was doing, audio editing, video editing. I coded my own website. I was doing my own outbound sequencing. I was doing my own graphic design, my own copywriting, and people be, oh my God, that’s so much. How did you figure that out? By watching YouTube videos on how to do all this shit. It wasn’t that complicated. I just spent a lot of time being curious.
And you asked, is that work fun? No, none of that work is fun. Like, what’s fun is this, this is like the fun part of the work. Like nobody likes coding a website. I mean, like, I don’t, I don’t like it.
Chris: Somebody does, but it ain’t, but it ain’t us, Scott. Somebody does.
Scott: You know how boring video editing is? Like, there’s some people that love it. I hate it. I can’t stand it. It’s so time consuming. So I’m curious. I learn all the skills. I do a whole bunch of shitty work, but I’m doing it in pursuit of something that means a lot to me.
So the podcast means a lot to me because, for a few reasons. I mean, I get to have great conversations every time I interview somebody, I learn a lot. It’s my own business. It also, checks the box of, if I’m going to build a business, I could build a business around a lot of different things. I love teaching. I love teaching, and the podcast sort of checks that box. For some reason, that just lights me up even when I was very young, my first, first job ever was coaching tennis. And, to watch somebody transform from really not knowing what they’re doing, to being pretty good at something that gives me so much energy. And I’ve just found that a good way to figure out if the path you’re on is the right path, outside of asking all these questions, a simple question is, does this give me energy?
Does this light me up? And if not, then maybe you’re not doing the right thing. But the podcast gives me tons of energy. I love it. I check the box of teaching people that gives me tons of fulfillment. So great, that’s the goal that I’m going after. But most of the work in pursuit of that goal is not fun work.
So I don’t think you have to love the work at all. I think you have to love the goal. And if you love the goal enough, the work doesn’t matter.
Todd: You’ll do the work. Yeah. I mean, like in our, in our community, we have six core principles of how to reinvent your career, and we’ve talked about them all today, that you’ve just reiterated so many of them, like getting clarity about what you want. That’s what we call our North Star. Like where do you want your North Star to be getting a game plan in place, taking action, right? Building new skills. Like all these things that we talked about today, are just incorporated in how we’re helping these mid-career folks do it. And I just wanna say, it’s refreshing and it makes me feel more confident in what we’re presenting to our folks because a lot of this work is just some mental and behavioral reprogramming, like I said in the
Scott: That is all it is.
Todd: That’s all it is.
Scott: The biggest issue that your community is gonna have is sunk cost fallacy. That is the biggest problem. They think that they put so much time into their career already that, oh my God, I I can’t reinvent myself now. I’ve put 20 years. Great.
Todd: So gimme a sentence or two right now to debunk that. Like what would you say to that? How do we combat that?
Scott: Okay, so let’s say you’re, 45, Okay. So to build something impressive, to build something that it’s making good money. I would say on average it takes between seven to 12 years. I think that’s a pretty safe bet. If you podcast for 10 years, you will have a bigger podcast than most people.
And it’s not gonna be Joe Rogan. Maybe it could be, but you’ll have a very strong community. You’re not just podcasting and not paying attention to the data, and you’re not paying attention to what increases your listen or retention, and you’re not paying attention to what topics do better or do worse.
You’re paying attention to all those things. You’re constantly moving in the right direction. So just through the process of committing a certain amount of time to something and putting in the reps, it’s going to become quite good.
Most businesses and most people that commit to something for, again, 10 plus years, they find a way to become pretty proficient at it. And that thing generates a lifestyle for them that far exceeds what usually, you know, you ever thought possible. I think that when you understand that timeframe, that it makes reinvention a lot less scary because even if you are 45, I’m telling you that if you commit to something for 10 years, you’re gonna find a way to make it successful and it’s gonna make you more money than y our job. It could be a podcast. It could be just selling your skills to the market, which is a great way to reinvent yourself and become an entrepreneur. You’re good at sales, you’re good at HR, you’re good at finance. The market will always pay you more for your skills than a company will.
That’s significantly more. You can carve out a great little lifestyle for yourself, doing basically what you do in your job and just selling it to the market. And you’ll probably make 10 x what you made in your job. And if you move towards that being your end goal for 10 years, I have absolute confidence you’ll find a way to make it work.
So why am I using this 10 year measuring stick? Because 10 years seems like a lot, but if we actually look at it, okay, so you’re 45, you’ve built a business that makes you more money than you really know what to do with by 55. is that really that scary?
Todd: You, know what I’ve also found, I love that you extended the timelines to that level, and here’s why. Here’s what I found in my journey of being an entrepreneur, coaching a lot of entrepreneurs, is that when you extend the timeline, it does something where it relaxes you either subconsciously or consciously, and you actually hit the successes faster as opposed to, I need to make this work in the next six months. By which that what you said in the beginning, now you’re working off emotional levers and emotional fears that are making you make bad decisions for the most part. So we train people to actually think a little bit longer term so that way they can actually have more relaxation so they can be soberly, making decisions along the way so that that 10 years becomes five years or even less.
Scott: You’re very accurate. I always hesitate to speak about this because I don’t want to accidentally skew their expectations. Right. I don’t want them to be like, Hey, when you chill out, you’re actually gonna move a lot quicker. And they’d be like okay. So now I can move a lot quicker, so now I can actually quit my job.
Chris: You gotta trick them, yeah
Todd: There’s something about that, right?
Scott: You’re right, because, I didn’t have the wisdom to understand that when I first started my podcast. I just said, I’m gonna do it for the rest of my life. That’s the promise I made to myself. And, uh, we’ve been doing the podcast now, for about seven years and it’s killing it. So I think that for some reason people just look at like a 10 or 15 year goal and they’re like, oh my God, my life’s over. Even though you’ve committed like 25 years to this career that you don’t like, and as opposed to exponentially growing, which is what happens in a business when you find true product market fit.
When you find true product market fit, you figure out, whatever the product is. It could be your knowledge, it could be an actual product, and then you figure out who your customer is, and then you figure out your, your customer acquisition cost to LTV ratio and you start to go down this rabbit hole and you learn about, everything to do with building a business, your growth is exponential. Meanwhile, your company’s giving you an extra 10 grand per year on top of your salary and they’ve been doing that for 25 years, so great. You’re making 300 grand, but you can’t, you can’t write off anything. You’re, you’re also just kind of capped out at what that company can pay you. Whereas if you just built a business for the last 25 years, even if it’s not one that makes, you know, the INC whatever list, it doesn’t matter. You’re making 2 million bucks a year, high margin, killing it. Like, you know, you have absolute freedom. You can work from anywhere in the world.
And by the way, 25 years to make $2 million a year is not that crazy. And for most people, maybe outside of living in Manhattan, 2 million bucks a year is, again, more money than they really know what to do with. I think people always think, well, I gotta have a big exit. I gotta raise. No, no, you don’t. You gotta find a business that works for you, and you gotta understand what you want your life to look like, and people actually don’t need as much money as they think they do in most cases. And then you start building towards that. And then all of a sudden your life looks radically different and you’re actually happy and fulfilled and you feel free, and, it just takes 10 to 15 years to accomplish this. But again, nobody ever starts. So it’s like you just keep pushing it back, keep pushing it back, keep pushing it back. You never start this 10 year clock. And that’s what it would take.
Or what people do is they quit their job and then they have like a six month timeline and they have to go back to their job because they ran outta money. Also stupid. Dude in the age of AI, and not just AI. Like if you, if you are a fan of, Naval Ravikant, there’s a Twitter thread about, the four kinds of leverage, right? You have tech, you have financial leverage, you have human leverage, and then you have media leverage. And if you understand those kinds of leverage, you can totally build a very successful business from five to nine and on the weekends, if you understand how to use AI and agents, if you understand how to build a brand around yourself to attract customers, if you understand, how to even, you know, recruit help in different parts of the world and work asynchronously.
And then the last piece, which I don’t even think is as impactful as it used to be, is financial. If you have to raise, you can raise, but I think the point is with the amount of resources and leverage we have access to now, we can build a pretty massive business. Maybe massive in the tens of millions, but a pretty massive business just for ourselves, even in like the seven figure range, when we have free time and spare time if we commit enough years to that thing. So I think that that sort of reframes, reinvention and it makes it a lot more achievable and it makes it less of like this fever dream that’s, this future distant thing that I wish I could do it, but maybe entrepreneurship is not for me.
Like all these like, limiting beliefs that people have, whatever it is, and it makes it a lot more attainable, when we start to look at it with some of the mental models that we’ve spoken about today.
Chris: The key there, right? And it’s like we could say seven years, 10 years, whatever the key is the commitment. The key is that I’m committed to this, I’m gonna go down this road again. You don’t actually necessarily know what it’s gonna look like in 10 years exactly.
But it’s the commitment. And you know, the analogy I always make is you’re standing on this side of the chasm and you wanna jump to the other side of the chasm.
Well, the one thing you can’t do is half jump you, half jump, that’s when you fall down in the pit. Right? So you have to really commit. And I think that to me is the most important part of this. It goes through all the things we talked about, the belief, you know, talking about your own career, you believed you would make it work, but you didn’t know 100% what that would look like.
The belief keeps driving you and the commitment keeps driving you. And that’s that inevitability.
Scott: A hundred percent. And this is what I’ve applied to my own life. And by the way, there’s an important thing I wanna touch on. I mentioned that I tried a whole bunch of things that didn’t work. They didn’t work because it was impossible for me to make them work. Like I shut those things down because I felt like they weren’t what I actually wanted to build. I wouldn’t have been happy if, for whatever reason, maybe it was work-life balance, maybe it was wrong partner. Maybe it was something that I just wasn’t excited about. Like for whatever reason, I knew that if I put more time and energy and attention towards that thing, I could make it work, but I didn’t want to make it work.
So I don’t look at those things as failures. I look at those things as decisions.
Because I truly believe that if you do want to do any of the things that I mentioned that I’m not working on anymore, I could have figured it out. I’m not an idiot. Most of the people listening to this podcast are not idiots.
Like we can navigate the things that set us back, but sometimes you don’t want to, which is fine. That’s when you can shut it down.
I don’t think there’s a single business on earth that you couldn’t make work to some degree if you put enough energy towards it.
Todd: Yeah. I love it, man.
And by the way, we’re kind of coming up at time here. You’ve been so generous with the time and, one last question. I’m just curious, like, what’s next for you? What’s on the horizon? I mean, you got a podcast that has a hundred million downloads. Unbelievable, right? Like you have your agency that you’re building right now. Like, so now that you’re, you’re at this level of success, what are you looking out towards? Like, what is getting you really excited about the future?
Scott: You know, it’s funny, you asked before, to drop some lessons from people that, that have been on the show, and, just to drop names, I’ve, had conversations with like Gary V and Ryan Serhant and Seth Godin and Marc Randolph, who’s like the co-founder of Netflix.
And like, I’ve had conversations with some really, really incredible people and it’s hard for me to say this idea came from this person because they all believe all these ideas.
Todd: Mm-hmm.
Scott: Like they don’t all call them the same thing, but ultimately if you dive into any of their belief systems, they align with everything we spoke about, like a hundred percent of it.
That’s sort of my lead up to answer your question. So what’s next for me? Ironically is also what I think is, what a lot of people who achieve massive amounts of success. I’m not talking about like a, a podcast like, you know, people that have built companies worth billions and, and then some. They all look at success as how do I make sure that the rest of my life doesn’t fall apart in pursuit of the main goal?
Right? And, and the main goal for a lot of us is financial. It’s like, how do I build a business? How do I make more money? And I think that I feel the same way. So when I look at success and what I have planned for the future, I’m super excited about the podcast. I’m super excited about building this agency, which we didn’t really talk about it, but the reason why I killed a lot of the other things that, you know, quote unquote didn’t work out is because I didn’t feel like they were in alignment with what I was building. So I had like this podcast on one side, and then I was building all these like, random little businesses over here, and it was just my energy and attention was segmented into these two different buckets. So now, at least with what the work I’m doing, I have the podcast, I have an agency that basically does for people what I’ve done for myself.
So a lot more alignment, which just makes it easier to put attention towards it and energy towards it.
I’m excited about all that stuff, but what I’m really excited about is more personal things, to be quite honest. So, when you are a high achiever and when you’re building a lot, it’s really easy to let the rest of your life sort of fall apart.
So there’s sort of five buckets that I’ve figured out that are important to me that I think are important to most people. So obviously if your business success, but then you have, your physical health, your mental health, uh, your relationships, and then spirituality, whatever that looks like for you. So for me, I’m more focused on maintaining the other four things that I don’t wanna let take a back seat while I’m doing my work.
And I’ve structured my life on purpose to support the other parts of my life, if that makes sense. So a very real example, like what I’m excited about, you know, I just got engaged. We want to have kids get married. That’s super excited about that. That’s more meaningful than just another podcast episode. That’s sort of like the relationship bucket, right? Like carving out time for my health and wellness. That’s the spirituality, whatever. So segmenting time in my day for all these other things is important. Also, how I architect my life, I architect my life to support those other goals. I’m sitting in a podcast studio that’s in my backyard and I turned this little guest house into the studio and I could have like rented commercial space, you know, 30 minutes away.
I could have chosen to be one of those podcasters that like flies to a different city and interviews people. ’cause I would’ve had access to more people. To me that didn’t support balance that I’m trying to achieve in my life.
Chris: Amazing.
Scott: I have a lot of opportunities for that stuff that I don’t want to do because that’s not what I’m focused on.
So I always wanted to build something that would make a lot of money that would be successful, that I could be proud of, but it would still support the balance that I want in my life. And when I say balance, it doesn’t mean I don’t work hard.
Like I work exceptionally hard, but I also like working like five feet from my house.
That sort of serves my goal. So I think that, maybe this is a, another quick lesson. if you’re gonna reinvent yourself, you have to understand why you’re doing it? Sometimes I see people reinventing themselves and they’re like, oh, I need to make more money. I need to, you know, do more, build more whatever. And they don’t even realize that the people that are closest to ’em don’t really need that.
So you’re actually like doing it and you’re reinventing yourself almost selfishly. So if you are gonna reinvent yourself, like understand why you’re doing it and understand who you’re doing it for, and if you are doing it for yourself, that’s okay, but don’t just reinvent yourself to support a goal that no one else in your life cares about. If, the things that are important in your life are those people, because I think people, like they reinvent themselves. I gotta make more money. Now, all of a sudden you’re building a company, you’re never present, you don’t see your kids anymore, you’re traveling nonstop. ‘Cause you’re now an entrepreneur doing entrepreneur stuff and you’re making a little bit more money. But like your, your wife and your kids never sees you. Like, that’s also not a good reinvention.
Chris: You brought it all the way back really to the, where we started, like the why and asking that why am I doing what am I doing it for?
Scott: So that’s what I’m excited about in the future.
Chris: That’s such beautiful answer, man. I love, I love that that’s the answer
Todd: speaking our language there too, right?
Chris: Oh yeah. It’s so life and heart centered and, and beautiful. And it is like what are we doing this whole thing for? The business and the financial success is important, but it’s the life.
Scott: Yeah, exactly.
Todd: L ook, we’re both dads, you know, it looks like congratulations on getting engaged. You know, I’ve been with my wife for a while, Chris has too. And, uh, I can kind of see the future in front of you. And let me tell you, man, like that’s gonna be a fun journey for you
Scott: Thank dude. I appreciate
Todd: There’s nothing better. I tell you man, there is nothing better than that. I just wanna thank you, man again for being here and giving us all this wisdom.
I love the way that ended. ‘Cause what you just shared was so aligned, like just the balance and not getting lost. It’s so easy to get on these treadmills and get lost and then end up, well, how did I get here? Right? And it’s a lot about that reprogramming. And I think what you brought is a very just honest, sober look at, hey, like, let’s be curious about what makes me happy.
Let’s not be afraid to take risks either. Let’s not be afraid to make changes that you embody that it was very almost surreptitious in the conversation, but you’ve changed and pivoted a lot, within all your reinventions and like, that’s a real skill. Like you’ve been able to let go of stuff, and then try new stuff.
Probably faster than most. Like the fail fast Silicon Valley thing I think is like embedded in your DNA. I mean, we could go off on a million different tangents here, but I just wanna say man, like super grateful for this time.
Chris: Thank you so much
Scott: I’m grateful, thank you guys.
Todd: Following you along and I think this is gonna be really helpful for our audience and, uh, any last words from you before we sign off?
Scott: No, I, I appreciate what you guys are doing and, I hope that people take some of these ideas, I think that’s like the main thing, right? Just don’t just listen to this. Like take some of these ideas, test one out next week and just take action and move in that direction and get back into alignment and be happy and just love your life. And that’s all I got.
Todd: Yeah.
Chris: Speaking our language, man. Thank you so much, Scott. Appreciate you, man.
Scott: Oh my pleasure guys.
